Synthesis of Bioactive Compounds from 3-Carene (II): Synthesis, Antifungal Activity and 3D-QSAR Study of (Z)- and (E)-3-Caren-5-One Oxime Sulfonates

Abstract

A series of novel (Z)- and (E)-3-caren-5-one oxime sulfonates were designed and synthesized in search of potent antifungal agents. The structures of the intermediates and target compounds were confirmed by UV-Vis, FTIR, NMR, and ESI-MS. The in vitro antifungal activity of the target compounds was preliminarily evaluated against Cercospora arachidicola, Physalospora piricola, Alternaria solani, Rhizoeotnia solani, Bipolaris maydis and Colleterichum orbicalare at 50 µg/mL. The bioassay results indicated that the target compounds exhibited the best antifungal activity against P. piricola, in which compounds 4b, 4f, 4m, 4e, 4j, 4l, 4y, 4d, and 4p had excellent inhibition rates of 100%, 100%, 100%, 92.9%, 92.9%, 92.9%, 92.9%, 85.7%, and 85.7%, respectively, showing much better antifungal activity than that of the commercial fungicide chlorothanil. Both the compounds 4y and 4x displayed outstanding antifungal activity of 100% against B. myadis, and the former also displayed outstanding antifungal activity of 100% against R. solani. In order to design more effective antifungal compounds against P. piricola, the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) was carried out using the CoMFA method, and a reasonable and effective 3D-QSAR model (r2 = 0.990, q2 = 0.569) has been established.

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

“…Sulfonate derivatives, owing to physicochemical properties, have a strong affinity for lipid phases and can cross the cuticle membrane easily to bind to target sites [23], and compounds containing aryl sulfonate moieties have received considerable attention due to extensive biological activities, and it has been proven to possess antiviral [24,25], antibacterial [26][27][28], insecticidal [29,30], anticancer [31,32], and other biological activity [33]. They were widely used in agricultural industries, medicine researches and other fields.…”

Synthesis, 3D-QSAR and Molecular Docking Study of Nopol-Based 1,2,4-Triazole-Thioether Compounds as Potential Antifungal Agents

“…In continuation of our interest in developing natural product-based bioactive compounds ( Lin et al, 2017 ; Wang X. et al, 2018 ; Lin et al, 2018 ; Kang et al, 2019 ; Liu et al, 2020 ; Zhu et al, 2020 ; Chen et al, 2021 ; He et al, 2021 ), a series of novel nopol derivatives containing 1,2,4-triazole and thioether moieties were designed and synthesized by the strategy of molecular docking-based virtual screening based on the crystal structure of cytochrome bc 1 complex. In addition, a three-dimensional structure-activity quantitative relationship (3D-QSAR) model was established by the comparative molecular field analysis (CoMFA) method.…”

Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds

“…In continuation of our long-term focus on natural product-based bioactive compounds [ 28 , 29 , 30 , 31 , 32 ], a series of novel nopol-derived 1,3,4-thiadiazole-thiourea compounds were synthesized by integrating bioactive 1,3,4-thiadiazole and thiourea moieties into the molecular skeleton of nopol. Structural characterization, antifungal evaluation, and structure–activity relationships of the title compounds were determined as well.…”